GB939708A - Production of ª -hydroxybenzylpenicillin - Google Patents
Production of ª -hydroxybenzylpenicillinInfo
- Publication number
- GB939708A GB939708A GB1975661A GB1975661A GB939708A GB 939708 A GB939708 A GB 939708A GB 1975661 A GB1975661 A GB 1975661A GB 1975661 A GB1975661 A GB 1975661A GB 939708 A GB939708 A GB 939708A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxybenzylpenicillin
- mandelic acid
- acid
- penicillin
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 3
- 108010073038 Penicillin Amidase Proteins 0.000 abstract 2
- MAGPZHKLEZXLNU-UHFFFAOYSA-N mandelamide Chemical compound NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 241000588724 Escherichia coli Species 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229960002510 mandelic acid Drugs 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/60—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
a -Hydroxybenzylpenicillin is produced by reacting 6-aminopenicillanic acid with mandelic acid or a salt or derivative thereof at pH not exceeding 9 in the presence of a penicillin amidase enzyme preparation derived from a penicillin amidase-producing bacterium such as Escherichia coli and subsequently recovering the a -hydroxybenzyl-penicillin. Mandelic acid derivatives which may be used include mandelamide, mandelic acid esters and a -hydroxyphenol-acetylthioglycollic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1975661A GB939708A (en) | 1961-06-01 | 1961-06-01 | Production of ª -hydroxybenzylpenicillin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1975661A GB939708A (en) | 1961-06-01 | 1961-06-01 | Production of ª -hydroxybenzylpenicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB939708A true GB939708A (en) | 1963-10-16 |
Family
ID=10134695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1975661A Expired GB939708A (en) | 1961-06-01 | 1961-06-01 | Production of ª -hydroxybenzylpenicillin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB939708A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4135978A (en) * | 1977-08-19 | 1979-01-23 | Merck & Co., Inc. | Production of n-acyl-thienamycins |
| US4162193A (en) | 1977-08-19 | 1979-07-24 | Merck & Co., Inc. | Enzymatic cleavage of N-acyl-thienamycins |
-
1961
- 1961-06-01 GB GB1975661A patent/GB939708A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4135978A (en) * | 1977-08-19 | 1979-01-23 | Merck & Co., Inc. | Production of n-acyl-thienamycins |
| US4162193A (en) | 1977-08-19 | 1979-07-24 | Merck & Co., Inc. | Enzymatic cleavage of N-acyl-thienamycins |
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